Triphenylphosphine → 5,7-dimethyl-2-ethyl-3-[4-tert-butyldimethylsilyloxy-3,5-dipropylphenyl]methyl-3H-imidazo[4,5-b]pyridine

HRID 2399516Notes

Reaction equation

HRID 2399516 reaction equation
[Si:1]([O:8][C:9]1[C:16]([CH2:17][CH2:18][CH3:19])=[CH:15][C:12]([CH2:13]O)=[CH:11][C:10]=1[CH2:20][CH2:21][CH3:22])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:23][C:24]1[N:29]=[C:28]2[N:30]=[C:31]([CH2:33][CH3:34])[NH:32][C:27]2=[C:26]([CH3:35])[CH:25]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:23][C:24]1[N:29]=[C:28]2[N:30]([CH2:13][C:12]3[CH:15]=[C:16]([CH2:17][CH2:18][CH3:19])[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[C:10]([CH2:20][CH2:21][CH3:22])[CH:11]=3)[C:31]([CH2:33][CH3:34])=[N:32][C:27]2=[C:26]([CH3:35])[CH:25]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 98153742,6-Dimethyl-8-ethyl-1-deazapurineHCID 19080464(4-{[tert-Butyl(dimethyl)silyl]oxy}-3,5-dipropylphenyl)methanol

Product 1

HCID 193856855,7-dimethyl-2-ethyl-3-[4-tert-butyldimethylsilyloxy-3,5-dipropylphenyl]methyl-3H-imidazo[4,5-b]pyridineYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4.2 g (13.0 mmol) of the product of Step E, 2.5 g (14.0 mmol) of 5,7-dimethyl-2-ethylimidazo[4,5-b]pyridine (Example 24, Step C), and 5.62 (20.0 mmol) of triphenylphosphine dissolved in 40 mL of THF, was added 3.396 g (20.0 mmol) of diethyl azodicarboxylate and the mixture was stirred for 1 hour. The reaction mixture was then concentrated in vacuo and the residual oil was purified on a silica gel flash chromatography column eluted with 25-40% ethyl acetate/hexane to afford 5 g (80%) of the title compound.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residual oil was purified on a silica gel flash chromatography column
  3. washeluted with 25-40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-94dfd01a16c140e59ab00957f0d6b60b
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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